Pyridine → HCID 9863078, compound

HRID 865372Notes

Reaction equation

HRID 865372 reaction equation
[NH2:1][CH2:2][CH:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[C:13]([F:15])[C:12]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)=[C:11]([F:22])[CH:10]=2)[CH2:4]1.N1C=CC=CC=1.[C:29](OC(=O)C)(=[O:31])[CH3:30]>C(Cl)Cl>[C:29]([NH:1][CH2:2][CH:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:10]=[C:11]([F:22])[C:12]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)=[C:13]([F:15])[CH:14]=2)[CH2:4]1)(=[O:31])[CH3:30]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 10040744HCID 10040744, compound

Product 1

HCID 9863078HCID 9863078, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(±)-5-(Aminomethyl)-3-[4-(3-pyridyl)-3,5-difluorophenyl]-2-oxazolidinone (PREPARATION 7, 135 mg, 0.433 mmol) in anhydrous methylene chloride (10 ml), pyridine (143 μl, 1.77 mmol, 4 eq) and acetic anhydride (167 μl, 1.77 mmol, 4 eq) are combined. The reaction is allowed to stir at 20°-25° under nitrogen. After 2.5 hr the reaction is added to methylene chloride (30 ml) and washed with saturated sodium bicarbonate then brine, dried (sodium sulfate), filtered and concentrated under reduced pressure to a solid. This material is purified by silica gel (70 g) chromatography eluted with methanol/chloroform (1/99-4/96 gradient). The appropriate fractions are pooled and concentrated to give the title compound, mp 218°-219°; FTIR (mull)cm-1 3347, 1742, 1679, 1648, 1563, 1409, 1247, 1022, 755; MS (EI, m/z) 347 [M+ ], 303, 275, 244, 219, 73, 56; NMR (CDCl3) 8.68, 8.59, 7.85, 7.48-7.41, 7.31, 4.87-4.79, 4.10, 3.82, 3.72-3.57, 2.03 δ.

Workup

  1. washwashed with saturated sodium bicarbonate
  2. dry with materialbrine, dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure to a solid
  5. customThis material is purified by silica gel (70 g) chromatography
  6. washeluted with methanol/chloroform (1/99-4/96 gradient)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4e39bfd5764c49d9b8436d978d9939ef
Source dataset
uspto-grants-1996_10
Patent number
US05565571

Reaction notes

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